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Cytotoxic Barrigenol-like Triterpenoids from an Extract of Cyrilla racemiflora Housed in a Repository.

ABSTRACT: Two new [(+)-cyrillins A (1) and B (2)] and four known barrigenol-like triterpenoids (3-6), along with betulinic acid and (+)-3?-O-trans-feruloylbetulinic acid, were isolated from a sample-restricted CH2Cl2-soluble extract of the bark of Cyrilla racemiflora, collected in Dominica. The structures of the new compounds were elucidated by interpretation of their spectroscopic data, and the absolute configuration of the cyclic 1,2-diol unit of (+)-cyrillin A (1) was ascertained by analysis of the electronic circular dichroism (ECD) spectrum induced with [Mo2(OAc)4]. In the case of (+)-cyrillin B (2), which was found to contain a diangeloylated glucose residue, the structure proposed was supported by analysis of its MS(2) and MS(3) spectra. All compounds isolated were evaluated for their cytotoxicity against HT-29 human colon cancer cells, and the known compound, (+)-barringtogenol B (3), was found to be the most potent, exhibiting an IC50 value of 1.7 ?M. This compound also showed inhibitory activity toward the CCD-112CoN human normal colon cell line, with an IC50 value of 5.9 ?M, indicating a lack of cytotoxic selectivity.

SUBMITTER: Ren Y

PROVIDER: S-EPMC4619146 | biostudies-literature | 2015 Oct

REPOSITORIES: biostudies-literature

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Cytotoxic Barrigenol-like Triterpenoids from an Extract of Cyrilla racemiflora Housed in a Repository.

Ren Yulin Y VanSchoiack Andrew A Chai Hee-Byung HB Goetz Michael M Kinghorn A Douglas AD

Journal of natural products 20150930 10

Two new [(+)-cyrillins A (1) and B (2)] and four known barrigenol-like triterpenoids (3-6), along with betulinic acid and (+)-3β-O-trans-feruloylbetulinic acid, were isolated from a sample-restricted CH2Cl2-soluble extract of the bark of Cyrilla racemiflora, collected in Dominica. The structures of the new compounds were elucidated by interpretation of their spectroscopic data, and the absolute configuration of the cyclic 1,2-diol unit of (+)-cyrillin A (1) was ascertained by analysis of the ele ...[more]

PMID: 26422131

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Project description:Lansium domesticum Corr. is a member of the Meliaceae family that is widely spread in tropical and subtropical region of Asia and America. Traditionally, the fruit of this plant has been consumed because of its sweet taste. However, the fruit peels and the seeds of this plant have been rarely utilized. The previous chemical investigation of this plant showed the presence of secondary metabolites with many biological activities, including cytotoxic triterpenoid. Triterpenoids is a class of secondary metabolites which contain thirty carbon atoms in the main skeleton. The high modification of this type of compound, including the ring opening, highly oxygenated carbons, and the degradation of its carbon chain to give the nor-triterpenoid structure, is responsible for its cytotoxic activity. In this paper, we isolated and elucidated the chemical structure of two new onoceranoid triterpenes, kokosanolides E (1) and F (2), from the fruit peels of L. domesticum Corr., along with a new tetranortriterpenoid, kokosanolide G (3), from the seeds of L. domesticum Corr. The structural determination of compounds 1-3 was undertaken through FTIR spectroscopic analysis, 1D and 2D NMR, mass spectrometry, as well as through a comparison of the chemical shifts of the partial structures of compounds 1-3 with the literature data. The cytotoxic properties of compounds 1-3 were tested against MCF-7 breast cancer cells using the MTT assay. Moderate activity was shown by compounds 1 and 3, with IC50 values of 45.90 and 18.41 μg/mL, respectively, while compound 2 showed no activity (IC50 168.20 μg/mL). For the onoceranoid-type triterpene, the high symmetrical structure of compound 1 is presumably the reason for its better cytotoxic activity compared with that of compound 2. Compound 3 showed moderate activity, mainly because of the presence of the furan ring, which, based on the literature, gives better cytotoxic activity in a tetranortriterpenoid-type structure. The findings of three new triterpenoid compounds from L. domesticum indicate the significant value of this plant as a source of new compounds.

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Cytotoxic Barrigenol-like Triterpenoids from an Extract of Cyrilla racemiflora Housed in a Repository.

Publications

Cytotoxic Barrigenol-like Triterpenoids from an Extract of Cyrilla racemiflora Housed in a Repository.

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